Protesters smashed a window at the Mission District Police Station, part of an angry reaction to an officer shooting a man.

Photo: Liz Hafalia, The Chronicle

Protesters smashed a window at the Mission District Police Station,...

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Marchers push through the Mission District, protesting a plainclothes police officer's shooting of an armed parolee.

Photo: Sarah Rice, Special To The Chronicle

Marchers push through the Mission District, protesting a...

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Steve Rebentisch, the head trainer at LiveFit Wellness Club on Valencia St., cleans up after protestors smashed windows at the business while marching through the Mission District to protest the police shooting of an armed 22-year old in San Francisco, Calif., Friday, September 21, 2012.

Photo: Sarah Rice, Special To The Chronicle

Steve Rebentisch, the head trainer at LiveFit Wellness Club on...

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Police line up on Valencia St. as protestors march through the Mission District on Friday evening.

A San Francisco police officer shot and wounded an armed 22-year-old parolee in the city's Mission District late Thursday, prompting a protest by dozens of people hours later, authorities said. Another group gathered in the area Friday night, vandalizing banks and a restaurant.

A plainclothes officer, part of a curfew enforcement team, shot the man after he allegedly pulled a Tec-9 assault-style pistol in the 200 block of 14th Street at 8:06 p.m. Thursday, police said.

The wounded man, whose name was not released, was taken to the hospital. Police said his injuries were not life-threatening. Police described him as a felon previously convicted of assault with a firearm.

According to Sgt. Michael Andraychak, a police spokesman, two gang task force police officers were working with two probation officers when they spotted a pair of men they recognized as gang members.

As one officer approached, Andraychak said, one of the suspected gang members fled, pulling a pistol as he ran.

As the suspect turned toward the officer and began to raise the pistol, the undercover officer opened fire, Andraychak said. The man was hit twice.

Police said the four officers were participating in Operation Night Light, described as an effort to ensure that juveniles on probation are off the streets and home after curfew, which differs from case to case. The man who was shot was not a juvenile on probation, said William Siffermann, chief juvenile probation officer.

Two hours after the shooting, several dozen people began protesting outside the Mission District Police Station on Valencia Street. During the protest, someone spray-painted graffiti reading "Killers" on the front doors of the station and damaged some windows, Andraychak said.

Employees at cafes and restaurants along Valencia said they saw dozens of police cars and officers in riot gear lining the street.

"It's always unsettling to see a bunch of cop cars and such, and around 15th and Valencia, there were just like 30 police cars," said Kimmy Watson, a manager at Bar Tartine restaurant on Valencia.

Anthony Strong, a chef at the nearby Locanda restaurant, described officers in riot gear gathering in the intersection of 16th Street and Valencia, facing east down 16th. Although he didn't see any protesters, he said onlookers were heckling the officers.

Resident Phil Deschaine said he saw the protesters eventually making their way down South Van Ness Avenue chanting, "F- the police," and "Do you feel safe?" as police cars and vans slowly trailed them.

Friday night, about 75 protesters gathered at Dolores Park, then headed down 18th Street, where they turned over outdoor tables at Farina restaurant.

They broke a window in the U.S. Bank at 16th and Mission and broke glass at the Wells Fargo near the 16th Street BART Station. They threw a bottle filled with what looked like paint at officers guarding the Mission Police Station.